Five Ways to Wear Olive Jeans + Fall Challenge Giveaway!

If there’s one sure bet for fall 2017 fashion, it’s got to be olive! This color is everywhere and even though it’s been around for a few seasons now, this fall seems to be it’s best showing yet. If you don’t have a pair of olive jeans, today’s post will hopefully convince you why now’s the time to buy.

Olive jeans are incredibly versatile (you can wear them like you would any neutral) and make outfits so much more interesting than ordinary denim.  Here are five of my favorite ways to wear olive jeans.

Five Ways to Wear Olive Jeans

1.  Stripes + Olive

This is quite possibly one of my favorite ways to pair up my olive jeans. Just add a striped top and a tassel necklace for an instant outfit!

Striped Bell Sleeve Top/Olive Jeans/Tassel Necklace (similar)/Gold Sandals

2.  Navy + Olive

Navy is another one of fall 2017’s hottest colors.  For a great fall transition look, pair up a navy top with olive jeans and rose gold accessories.

Navy Tee/Olive Jeans/Pendant Necklace/Earrings/Gold Sandals

3.  Burgundy + Olive

Burgundy is a fall staple that was made for olive jeans.  For date night layer a burgundy tee under a moto jacket, add ankle booties and a statement necklace.

Burgundy Tee/Moto Jacket/Olive Jeans/Statement Necklace/Earrings/Ankle Boots

4.  White Tee + Olive

A great white tee is a closet basic that you’ll use year round.  Layer one under a neutral cardigan and add a printed scarf to pull it all together.

White Tee/Olive Jeans/Cardigan/Printed Scarf/Sneakers (similar)

5.  Gray + Olive

Pair up a cozy gray sweatshirt with olive jeans and slip on sneakers for the perfect fall errand running outfit. Add a statement necklace for an unexpected bit of bling.

Gray Sweatshirt/Olive Jeans/Sneakers (similar)/Statement Necklace

Fall Challenge News and Giveaway

If you loved these outfits, then the Fall 2017 GYPO Style Challenge may be just what you’re looking for!  We’ll be styling most of these pieces and many others in our 25 days of mix and match outfits.  Registration opens this Friday, September 1st.

We will be donating 10% of sales from the fall challenge to the American Red Cross to help those affected by Hurricane Harvey.

If you’re new around here, I started the first Style Challenge in Spring of 2014 based upon feedback from a reader survey. You asked me to give you a shopping list of classic basics and seasonal trends that you could shop for on your own.  After putting together that first list, I took it one step further to create mix and match outfit ideas from the pieces on that list.  And the first capsule wardrobe was born!

Since then, nearly 10,000 women in 20 different countries have participated in a Style Challenge.

What it Is:

You’ve probably seen a lot of capsule wardrobe programs popping up lately but the GYPO Style Challenge is the first and original style challenge. You may be asking why pay for something you can find online for free. Well, none of those free programs provide you with as much support, detailed instructions and bonuses as the Style Challenge.

It’s called a challenge only because it “challenges” you to get out of your comfort zone to try new styles – there’s no competition!

Step 1: You get a shopping list of classic basics and seasonal trends with everything you need to create a mix and match capsule wardrobe. You have two weeks to get all of the pieces on the list. You’re free to spend as much or as little as you want but most women shop their closets first! I also provide you with a robust directory of online shopping links from stores you love. Plus we reuse pieces from past challenges so each season builds upon the others. After you participate once, you’re never starting from scratch!

Step 2: After those pieces are in place, you’ll get a daily outfit e-mail each day for 25 days showing you how to pair your pieces up into on-trend fall looks that work for your daily life. Imagine waking up every day and knowing EXACTLY what to wear! It makes getting dressed a no-brainer.

Step 3: Show off your new style in our private Facebook group. This is honestly the best part of the challenge! Thousands of women have made real life friends and explored style in this safe, supportive community of like minded women. We share shopping tips, fit advice and our own unique takes on the daily outfits. You will get SO much inspiration just from being in this group.

More Benefits:

Style Challenge Members Only Site – The original Style Challenge is the only one that includes access to the Style Challenges membership site. It’s a handy directory of resources and every Style Challenge you’ve ever purchased all in one place!

Recommended Items Directory – Inside the membership site is an online evergreen catalog of updated shopping links at a variety of price points to the stores you love most. This challenge’s Recommended Items Directory has more trend options than ever before. You’ll be able to shop more classic “basics” or substitute the trendier item for each piece on the list. These links are updated throughout the season so you always have resources for items to buy.


Daily Style Tips – Included with each outfit is a daily style tip to give you easy to implement tips on your style journey.


New for this Challenge!

If you’ve done the GYPO Style Challenge in the past, here are some new features you can expect this time around.

One Page Print Out of ALL Outfit – This makes it easier than ever to see at a glance every outfit in this capsule.  All 25 days of outfits are on a one page print out that you can hang in your closet for easy reference.

The GYPO Quarterly Closet Clean Up – A handy printable to make sorting your closet a breeze. Follow these instructions each season and you’ll always have a curated closet of pieces you LOVE and wear.

Bonus – Access eleven outfits immediately! You’ll be able to see the first 7 days of outfit plus the free four bonus outfits as soon as you sign up.

Dress it Up/Dress it Down Options – Each outfit includes tweaks to make it office appropriate or super casual for every day so you can get double the use.

Double the Outfits – You’ll also get access to Fall 2016’s outfits doubling your total outfits!

Weekly Gift Card Giveaways – Each week one lucky lady wins a $100 gift card to her choice of clothing store.

Everything You Get:

  • The shopping list of basics and on trend items. Start where you are. You don’t have to be a fashionista or have a closet full of clothes.
  • A daily outfit idea sent in your email every day for 25 days.
  • Daily style tips to go along with your outfits.
  • The supportive Facebook group of women just like you on the style journey. Some are ahead and some are just starting out. The beauty is in the advice and friendships shared!
  • Weekly clothing gift card giveaways to some of your favorite stores.
  • A complete mix and match capsule wardrobe that you can build upon each season!

Who It’s For:

  • Anyone stuck in a style rut who’s ready to rediscover confidence through easy style
  • Women looking for “ease” in their days and done for them outfit ideas.
  • Anyone willing to try new things and get out of the style comfort zone.

How Much is It:

If you’ve ever looked into a personal style service, you know they start at upwards of $150 for just one hour of advice! Because I believe in my heart that every women deserves access to great style and to feel pretty, I founded the GYPO Style Challenge on the concept that it should be affordable to all. All of the tools and resources in this program are available for just $39.

What are the important dates?:

Registration opens on Friday, September 1st so you have your shopping list in time for Labor Day sales. We start to style our first outfit on September 18th. You’ll have until then to get everything on the shopping list so I highly recommend signing up as soon as registration opens!

If you don’t have all of your items by then, don’t sweat it! You can always sit back and watch and curate the pieces as you find items you love.

The live portion of the challenge is from September 18th – October 12th. We’ll be styling our daily outfits each day during this time.

It’s Risk Free!

The best part?  You get to try it risk free!  If you sign up and decide it’s just not for you, you’ll have until September 23rd to request a refund.  As a gift, you can keep the first 11 days of outfit ideas just for trying it.


How Much Will I Need to Spend on the Shopping List Items?

That’s totally up to you.  Most women shop their closets first and find that they have quite a few items on the list already.  Some are starting from scratch.  I recommend that you set a budget to work within and find the pieces you absolutely love.  I also recommend that you take your time to curate the items on the list.  It’s better to wait for a piece that you’ll continue to wear and love than to rush to get all of them at once. Each seasonal capsule builds on other capsules so you should never have to do as much shopping as you do the first time.  Many women are able to completely shop their closets and add in just some fun trends after a few rounds.

Will this Work for My Weather?

Yes!  Women from all over the U.S., Canada and even Europe participate in the challenge and make it work for their climate. You’ll get so much inspiration just from joining the Facebook group.

What Style are the Outfits?

There’s a good mix of casual every day and dressy casual looks.  Every outfit includes a dress it up/dress it down option so that you can make your own tweaks to make it work for everything from a day at home to office appropriate.

Do I Have to Style them Every Day?

Nope!  You’re welcome to skip when you want to.  These outfits are just styling suggestions.  Some women choose to participate every day in the Facebook group while others prefer to sit back, watch and learn.  You’re also welcome to substitute some of your favorite pieces from your closet to avoid repetition.  The point of the challenge is to show you how to pair up your pieces in multiple ways.

If you have any other questions about the GYPO Style Challenge, feel free to e-mail me and ask away!

Fall 2017 GYPO Style Challenge Membership Giveaway

Three lucky ladies will win a complementary membership to the Fall 2017 GYPO Style Challenge.  Winners will be drawn and notified on Friday, September 1st.  Good luck!
a Rafflecopter giveaway

Getting my pretty on with Style Elixir , Jo Lynne Shane, and A Little Bit of Everything.

I Feel Pretty Link Up

It’s the day of the week at GYPO where we celebrate what makes us feel pretty. Whether it’s a new outfit, hairstyle, or makeup, the I Feel Pretty link up is about anything and everything that makes your life prettier. Even if you’re not a blogger, you can still play along. Just tell me what made you feel pretty this week in the comments.

There are just a few simple rules:

1. Follow GYPO. (Bloglovin‘, FacebookInstagram or Pinterest)
2. Link up your pretty post.
3. Link back to GYPO.
4. Visit other pretties.That’s it, now go have some fun!



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